Alyssa Milano attends the Warner Music Group Post-Grammy Party, unveiling a frothy ivory gown that’s a perfect-10 encapsulation of early-aughts glamour.
The red carpet at a post-Grammy party is a different beast from the main event—it’s where celebrities loosen up a bit, trading high-stakes couture for a style that’s a touch more personal. And in 2002, Alyssa Milano perfectly captured that mood. Her ivory mermaid gown is a masterclass in delicate, intricate detail. The dress, with its plunging V-neckline, features a lace overlay that creates a soft, almost ethereal texture. The silhouette is pure early 2000s, hugging her figure to the knees before flaring out into a soft, romantic ruffle at the bottom.
Milano’s accessories are minimal, yet intentional. She carries a small, sparkling gold clutch—a pop of metallic that provides a point of contrast—and wears strappy, open-toed heels, which were all the rage. Her hair, styled in a subtle updo with a single white flower tucked behind her ear, is a charmingly romantic touch. It’s a look that feels both classic and of its moment, a testament to an era when a simple, well-chosen dress could make a powerful statement.
Anne Hathaway unveils a cool, confident look on the set of The Devil Wears Prada 2, channeling off-duty editor-in-chief vibes—a sharp, almost-too-perfect-for-life dose of New York street style.
The streets of New York City are the ultimate runway, and on a breezy day in August 2025, Anne Hathaway was caught in her element. Her look is a playful wink to her past as Andrea Sachs, but with the high-fashion edge of someone who’s made it. She wears a crisp, oversized white shirt left untucked over a simple white skirt. It’s a silhouette that feels both relaxed and intentional, a quintessential summer uniform for a woman on the move. But the accessories tell the real story.
Hathaway pairs the white ensemble with a black Favorite Daughter the Jordan Belt , a bold line that breaks up the monochromatic palette and gives the outfit structure. Her choice of footwear—chunky black sandals—is a practical and stylish departure from the stiletto-wearing days of her character’s past. She carries a chic, black-and-white checkered tote, and her face is framed by a pair of sleek black Otra Hazel Sunglasses . The whole look is a testament to the power of thoughtful styling. The vibe is a little bit casual, a little bit high-fashion, and all-around perfect.
Alyssa Milano attends Usher’s 2002 birthday party in an effortlessly chic ensemble, fusing a high-slit slip dress with a playfully bohemian cardigan for a dose of turn-of-the-century cool.
The year 2002 feels like a lifetime ago, a moment when the red carpet was less about grand, theatrical couture and more about a certain kind of downtown, rock-star casual. This is the era Alyssa Milano navigates with an expert hand at Usher’s “A Night of Masquerade” at The Highlands Hollywood. She unveils a look that’s a perfect snapshot of the time: a sleek black slip dress, its classic silhouette given an edge with a high-cut slit that offers a glimpse of leg. The real story, though, is the contrast—the texture, the unexpected layering.
Over the slinky dress, she wears a chunky, dark knit cardigan. It’s not just a cover-up; it’s a stylistic statement. The open-weave texture and ragged edges lend a soft, lived-in quality to the otherwise polished look, a nod to the era’s bohemian leanings. Her accessories, too, are understated yet impactful. A chunky silver bracelet and delicate, barely-there strappy heels (a favorite of the period) ground the look, while her hair, a simple ponytail with loose, face-framing pieces, completes the vibe. It’s a study in balance: the sleek against the slouchy, the formal against the carefree.
